HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HCID 6072Erstellt: 26. Oktober 2026
2'-(beta-D-Glucopyranosyloxy)-4,'6'-dihydroxy-3-(4-hydroxyphe-nyl)propiophenon
PHLORIDZIN · phlorhizin · phlorizine · phloridzine · PHLORIDZIN DIHYDRATE · NSC 2833 · Floridzin · PHLORIZIN
https://huagongshe.com/de/chemical/6072
Identifikatoren & physikalische Daten
| CAS No. | 60-81-1 |
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| Summenformel | C21H24O10 |
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| Durchschnittliche Molmasse | 436,4 g/mol |
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| Monoisotopische Masse | 436,13694697 g/mol |
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| SMILES | O=C(CCc1ccc(O)cc1)c1c(O)cc(O)cc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
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| InChIKey | IOUVKUPGCMBWBT-QNDFHXLGSA-N |
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| PubChem CID | 6072 |
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| ChEMBL | CHEMBL245067 |
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| ChEBI | CHEBI:8113 |
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| DTXSID | DTXSID3075339 |
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| Lokaler Name | 2'-(beta-D-Glucopyranosyloxy)-4,'6'-dihydroxy-3-(4-hydroxyphe-nyl)propiophenon |
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Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
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| Polarare Oberfläche (TPSA) | 177 |
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| H-Brücken-Donoren | 7 |
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| H-Brücken-Akzeptoren | 10 |
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| Frei drehbare Bindungen | 7 |
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| Schwere Atome | 31 |
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| Formalladung | 0 |
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| Komplexität | 581 |
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| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
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| Lipide | Polyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212] |
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| Löslichkeit | 1 mg/mL at 22 °CDMSO (Slightly), Methanol (Slightly) |
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| Endocrine Disruptors | Potential endocrine disrupting compound |
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| Schmelzpunkt | 110.0 °C113-114 °C(lit.) |
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| Physical Description | Off-white powder[ChromaDex MSDS]Solid |
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| Collision Cross Section | 194.4 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]192.5 Ų [M+H]+ [CCS Type: TW |
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| Siedepunkt | 468.89°C (rough estimate) |
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| Dichte | 1.3178 (rough estimate) |
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| Brechungsindex | -54 ° (C=3.2, 95% EtOH) |
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| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
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| Aggregatzustand | Solid |
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| pKa (Säurekonstante) | 7.15±0.40(Predicted) |
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| Farbe | Light Yellow to Tan |
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| Merck | 14,7327 |
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| Hauptanwendungen | food and beverages |
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| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
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| InChIKey | IOUVKUPGCMBWBT-LKLLPNDVNA-N |
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| SMILES | C(C1C(=CC(O)=CC=1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)(=O)CCC1C=CC(O)=CC=1 |&1:9,10,11,13,15,r| |
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| LogP (Verteilungskoeffizient) | 0.452 (est) |
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| CAS Datenbank | 60-81-1(CAS DataBase Reference) |
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| EPA chemische Informationen | Phlorizin (60-81-1) |
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Sicherheit & Vorschriften
| Gefahrenübersicht | Intraperitoneal |
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| F | 3-10-23 |
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| Wassergefährdungsklasse (WGK) | 3 |
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| Zollcode | 29389090 |
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| RTECS-Nr. | UC2080000 |
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| R-Sätze (R) | 36/37/38 |
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| Gefahrensymbole | Xi |
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| Sicherheitshinweise (S) | 26-36 |
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| Lagerklasse | 11 - Combustible Solids |
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Anwendungen & Verwendung
Verwenden
Sodium-glucose cotransporter 1 (SGLT1) is a high affinity, low capacity transporter abundant in the small intestine, with some expression in the kidney as well. SGLT2 is a low affinity, high capacity transporter in the kidney that accounts for approximately 90% of glucose reabsorption into the blood stream. Selective inhibition of SGLT2 is a potential strategy for reducing plasma glucose levels as a treatment for diabetes. Phlorizin is a natural product, first isolated from the bark of apple trees, that reduces plasma glucose levels by blocking renal and intestinal glucose absorption through inhibition of SGLT1 and SGLT2. It competitively inhibits the initial rate of a-methyl-D-glucopyranoside (a-MDG) uptake in human COS-1 cells expressing hSGLT1 and hSGLT2 with IC50 values of 400 and 65 nM, respectively. In HEK293T cells expressing human SGLT1 and SGLT2, phlorizin exhibits Ki values of 140 and 11 nM, respectively, at 37°C.